CN111596523A - Coloring composition and coloring resist composition - Google Patents

Coloring composition and coloring resist composition Download PDF

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Publication number
CN111596523A
CN111596523A CN202010098247.7A CN202010098247A CN111596523A CN 111596523 A CN111596523 A CN 111596523A CN 202010098247 A CN202010098247 A CN 202010098247A CN 111596523 A CN111596523 A CN 111596523A
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pigment
composition
group
colored
present
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辻康人
米田善纪
中川朋树
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Sakata Inx Corp
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Sakata Inx Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133512—Light shielding layers, e.g. black matrix
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
    • H10K50/865—Arrangements for improving contrast, e.g. preventing reflection of ambient light comprising light absorbing layers, e.g. light-blocking layers

Abstract

The invention provides a coloring composition capable of obtaining a black resist pattern with excellent light shielding performance and solvent resistance, and a coloring resist composition containing the coloring composition. The present invention relates to a coloring composition characterized by comprising a pigment and a binder resin, and the pigment comprises: at least one selected from the group consisting of c.i. pigment orange 16 and c.i. pigment yellow 139, and c.i. pigment blue 60.

Description

Coloring composition and coloring resist composition
Technical Field
The present invention relates to a colored composition and a colored resist composition containing the same.
Background
In recent years, a coloring composition for a black matrix (also referred to as a "black matrix") has been used in various applications, for example, in a flat panel display such as a liquid crystal display or a plasma display, a gap of a coloring pattern in a display region of a screen and an edge of a peripheral portion of the display region, and in a liquid crystal display using a TFT, a light-shielding film (black matrix) is provided on an external light side of the TFT. In addition, the liquid crystal display is mainly used for preventing light leakage from a backlight, and the plasma display is mainly used for preventing bleeding on a writing screen due to confusion of light of each color, thereby improving display characteristics (contrast and color purity).
For example, a color filter used to convert white light of a backlight of a liquid crystal display into colored light is generally manufactured by forming pixels of different hues of red, green, and blue in a pattern such as stripe or mosaic on a surface of a transparent substrate such as glass or a plastic sheet on which a black matrix is formed.
In addition, in a touch panel in which an image display device and a position input device are aligned, a color filter formed with a black matrix is used as a light shielding film in the same manner, and is generally formed on the side opposite to the sensor substrate with a glass cover interposed therebetween. However, as the demand for weight reduction of the touch panel increases, in order to achieve further weight reduction, a technology for forming the light shielding film and the touch sensor at the same time on the same side as the glass cover plate is being developed.
For example, patent document 1 discloses the following technique: in the photosensitive coloring composition for forming a color spacer, a specific pigment and carbon black are used in combination as a colorant, and the content ratio of the carbon black is set to a specific range, thereby imparting a masking property and the like.
Further, for example, patent document 2 discloses the following technique: by appropriately combining pigment types having different light absorption characteristics and ensuring a balance between light absorption in the ultraviolet region and light absorption in the visible region, the light-shielding property and the voltage holding ratio of the liquid crystal are maintained.
However, when the solvent resistance of a coloring composition (for example, a black matrix) constituting a liquid crystal layer of an image display device is low, there is a problem that a pixel pattern is broken or chipped or a coloring component is eluted from the pixel pattern.
In the above-mentioned techniques, no studies have been made on solvent resistance, and development of a black matrix coloring composition capable of obtaining a black resist pattern excellent in solvent resistance has been desired.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2016-177190
Patent document 2: international publication No. 2013/115268 handbook
Disclosure of Invention
Problems to be solved by the invention
Accordingly, an object of the present invention is to provide a colored composition capable of providing a black resist pattern having excellent light-shielding properties and excellent solvent resistance, and a colored resist composition containing the same.
Means for solving the problems
The present inventors have found that a coloring composition capable of producing a black resist pattern having excellent masking properties and excellent solvent resistance by using a specific pigment in combination in a coloring composition comprising a pigment and a binder resin can be obtained, thereby completing the present invention.
That is, the present invention relates to a coloring composition for a black matrix, which comprises a pigment and a binder resin, wherein the pigment comprises: at least one selected from the group consisting of c.i. pigment orange 16 and c.i. pigment yellow 139, and c.i. pigment blue 60.
Preferably, the pigment further contains at least one selected from c.i. pigment violet 23 and c.i. pigment violet 29.
Further, the present invention is also a colored resist composition produced by using the colored composition of the present invention.
The present invention also relates to a colored composition of the present invention or a colored resist composition of the present invention, which is used as a black matrix, a black column spacer, or a black partition material.
The coloring composition of the present invention and the colored resist composition containing the same are described in detail below.
(pigment)
For the coloring composition of the present invention, the pigment includes: at least one selected from the group consisting of c.i. pigment orange 16 and c.i. pigment yellow 139, and c.i. pigment blue 60.
By using the pigment, a coloring composition for a black matrix having excellent light-shielding properties and solvent resistance can be obtained. From the viewpoint of imparting solvent resistance, it is preferable that the above pigment contains c.i. pigment yellow 139 and c.i. pigment blue 60.
From the viewpoint of light-shielding properties, the content of the one or more pigments selected from the group consisting of c.i. pigment orange 16 and c.i. pigment yellow 139 is 5 to 60 mass%, more preferably 8 to 50 mass%, still more preferably 10 to 45 mass%, and particularly preferably 10 to 40 mass% based on the total amount of the pigments.
From the viewpoint of light-shielding properties, the content of the c.i. pigment blue 60 is preferably 5 to 70 mass%, more preferably 10 to 60 mass%, even more preferably 15 to 55 mass%, and particularly preferably 20 to 50 mass% with respect to the total mass of the pigment.
Preferably, the pigment further contains one or more selected from c.i. pigment violet 23 and c.i. pigment violet 29.
By making the above pigment further contain at least one selected from c.i. pigment violet 23 and c.i. pigment violet 29, excellent shielding properties are imparted to the black resist pattern obtained from the coloring composition.
From the viewpoint of imparting solvent resistance, the pigment preferably contains CI pigment violet 29.
From the viewpoint of light-shielding properties, the content of the one or more pigments selected from the group consisting of c.i. pigment violet 23 and c.i. pigment violet 29 is 1 to 70% by mass, more preferably 10 to 60% by mass, based on the total amount of the pigments.
In the coloring composition of the present invention, the pigment is preferably 20 to 90% by mass, more preferably 30 to 80% by mass, in terms of mass fraction, relative to the total solid content.
In the coloring composition of the present invention, the pigment may contain other pigments such as carbon black, red pigment, orange pigment, blue pigment, and green pigment as long as the effects of the present invention are not impaired.
(Binder resin)
The coloring composition of the present invention contains a binder resin.
The binder resin is not particularly limited as long as it is a resin that can be used for a member of a color filter, and examples thereof include an alkali-soluble resin, a thermosetting resin, a thermoplastic resin, a photopolymerizable compound (a photopolymerizable resin, a monomer having 1 or more photopolymerizable unsaturated bonds in the molecule, an oligomer, and the like), and the like. These may be used alone or in combination of two or more.
In the coloring composition of the present invention, the binder resin is preferably 1 to 40% by mass, more preferably 3 to 25% by mass, in terms of mass fraction, relative to the total solid content.
As the alkali-soluble resin, an alkali-soluble copolymer, an alkali-soluble Cardo resin, and the like can be exemplified.
As the alkali-soluble copolymer, for example: a copolymer obtained by reacting a carboxyl group-containing unsaturated monomer such as acrylic acid, methacrylic acid, itaconic acid, maleic anhydride, monoalkyl maleate, citraconic acid, citraconic anhydride, or monoalkyl citraconate with at least one member selected from the group consisting of styrene, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, glycerol monoacrylate, glycerol methacrylate, mono (meth) acrylate having a dicyclopentadiene skeleton, N-phenylmaleimide, a polystyrene macromonomer, and a polymethyl methacrylate macromonomer; and, epoxy acrylate resins.
As the alkali-soluble Cardo resin, there may be mentioned: and acid adducts of epoxy (meth) acrylates having a fluorene skeleton, which are addition products of fluorene epoxy (meth) acrylic acid derivatives and dicarboxylic anhydrides and/or tetracarboxylic dianhydrides.
The alkali-soluble resins described above may be used alone or in combination of two or more. From the viewpoint of film formability and alkali developability, the alkali-soluble resin preferably has an acid value of 40 to 200mgKOH/g and a weight-average molecular weight of 1000 to 5 ten thousand.
The alkali-soluble resin may be used in combination of one or two or more kinds as appropriate depending on the required properties.
Examples of the thermosetting resin or the thermoplastic resin include: butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyurethane-based resins, phenol resins, polyester resins, acrylic resins, alkyd resins, styrene resins, polyamide resins, rubber-based resins, cyclized rubbers, epoxy resins, cellulosics, polybutadiene, polyimide resins, polyamideimide resins, benzoguanamine resins, melamine resins, urea resins, and the like.
As the photopolymerizable resin, a resin obtained by introducing a photocrosslinkable group such as a (meth) acrylic compound or cinnamic acid into a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group via an isocyanate group, an aldehyde group or an epoxy group can be used. Further, a polymer obtained by half-esterifying an acid anhydride-containing linear polymer such as a styrene-maleic anhydride copolymer or an α -olefin-maleic anhydride copolymer with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate can be used.
In the photopolymerizable compound, examples of the monomer having 1 photopolymerizable unsaturated bond in the molecule include: alkyl methacrylates or alkyl acrylates such as methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, methyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate; aralkyl methacrylate or aralkyl acrylate such as benzyl methacrylate and benzyl acrylate; alkoxyalkyl methacrylates or alkoxyalkyl acrylates such as butoxyethyl methacrylate and butoxyethyl acrylate; aminoalkyl methacrylates or aminoalkyl acrylates such as N, N-dimethylaminoethyl methacrylate and N, N-dimethylaminoethyl acrylate; methacrylic acid esters or acrylic acid esters of polyalkylene glycol alkyl ethers such as diethylene glycol ethyl ether, triethylene glycol butyl ether, and dipropylene glycol methyl ether; methacrylic acid esters or acrylic acid esters of polyalkylene glycol aryl ethers such as hexaethylene glycol phenyl ether; isobornyl methacrylate or acrylate; glycerol methacrylate or glycerol acrylate; 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate, and the like.
In the photopolymerizable compound, examples of the monomer having 2 or more photopolymerizable unsaturated bonds in the molecule include: bisphenol A dimethacrylate, 1, 4-butanediol dimethacrylate, 1, 3-butanediol dimethacrylate, diethylene glycol dimethacrylate, glycerol dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol pentamethylacrylate, bisphenol A diacrylate, 1, 4-butanediol diacrylate, 1, 3-butanediol diacrylate, diethylene glycol diacrylate, glycerol diacrylate, neopentyl glycol diacrylate, Polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and the like.
(carbon Black)
The coloring composition of the present invention may contain carbon black from the viewpoint of adjusting the color tone.
Examples of the carbon black include acetylene black, channel black, furnace black, and ketjen black.
Specific examples of the Carbon black include MA7, MA8, MA11, MA14, #1000, #2350, etc., manufactured by Mitsubishi chemical corporation, Special Black350, Special Black250, Special Black550, NEROX2500, NEROX3500, NEROX305, MOGUL L manufactured by Cabot (CABOT), REGAL400R, TPK1101R, TPK1104R, TPK1227R, etc., RAVEN1200, RAVEN1250, RAVEN1255, RAVEN1190U, RAVEN1170, RAVEN1060, RAVEN1080U, RAVEN1060U, RAVEN1100U, etc., manufactured by Columbia Carbon black (Colombia Carbon).
Among them, acidic carbon black having an acidic group such as a carboxyl group at a pH of 5 or less is preferable. In addition, the particle size is preferably 20 to 60 nm.
Examples of the acid carbon black satisfying the above-mentioned requirement include NEROX2500, NEROX3500, TPK1101R, TPK1104R, TPK1227R and the like.
The particle size refers to an average primary particle size measured or calculated by microscopic observation.
The content of the acidic carbon black is not particularly limited, and is preferably 70% by mass or less based on the mass of the entire pigment in the coloring composition of the present invention. If the content of the acidic carbon black is more than 70% by mass, a decrease in voltage holding ratio or a decrease in exposure sensitivity may occur.
A more preferable upper limit of the content of the acidic carbon black is 50% by mass based on the mass of the entire pigment of the coloring composition of the present invention.
The coloring composition of the present invention may not contain the above-mentioned acid carbon black.
The coloring composition of the present invention further preferably contains a pigment dispersant, a pigment dispersion aid represented by the general formula (1) and/or (2) described later, and/or a pigment dispersion aid which is a sulfonated (optionally neutralized) product of copper phthalocyanine, and/or a pigment dispersion aid which is a sulfonated (optionally neutralized) product of c.i. pigment yellow 138, a binder resin, and an organic solvent.
(pigment dispersant)
The coloring composition of the present invention preferably contains a pigment dispersant.
The pigment dispersant is a basic group-containing pigment dispersant, and examples thereof include an anionic surfactant, a basic group-containing polyester pigment dispersant, a basic group-containing acrylic pigment dispersant, a basic group-containing polyurethane pigment dispersant, a basic group-containing carbodiimide pigment dispersant, and an acidic group-containing polymer pigment dispersant.
These basic group-containing pigment dispersants may be used alone, or two or more kinds of them may be used in combination. Among them, a basic group-containing polymeric pigment dispersant is preferable from the viewpoint of obtaining good pigment dispersibility.
Specific examples of the basic group-containing polymeric pigment dispersant include:
(1) a reaction product of an amino group and/or an imino group of a polyamine compound (e.g., a poly (lower alkylene amine) such as polyallylamine, polyvinylamine, and polyethyleneimine), and at least one selected from a polyester, a polyamide, and a polyesteramide having a free carboxyl group (Japanese patent application laid-open No. 2001-59906);
(2) reaction products of low-molecular-weight amino compounds such as poly (lower) alkyleneimine and methyliminodipropylamine, and polyesters having free carboxyl groups (JP-A-54-37082 and JP-A-01-311177);
(3) a reaction product obtained by sequentially reacting an isocyanate group of a polyisocyanate compound with a polyester group having 1 hydroxyl group such as an alcohol such as methoxypolyethylene glycol or a caprolactone polyester, a compound having 2 to 3 isocyanate group-reactive functional groups, and an aliphatic or heterocyclic hydrocarbon compound having an isocyanate group-reactive functional group and a tertiary amino group (Japanese patent application laid-open No. H02-612);
(4) a compound obtained by reacting a polymer of an acrylic ester having an alcoholic hydroxyl group with a polyisocyanate compound and a hydrocarbon compound having an amino group;
(5) a reaction product obtained by adding a low-molecular amino compound to a polyether chain;
(6) a reaction product obtained by reacting a compound having an isocyanate group with a compound having an amino group (Japanese patent application laid-open No. H04-210220);
(7) a reaction product obtained by reacting a linear polymer having a free carboxyl group with an organic amine compound having 1 secondary amino group (Japanese patent application laid-open No. H09-87537);
(8) a reaction product of a polycarbonate compound having a functional group capable of reacting with an amino group at one terminal and a polyamine compound (Japanese patent application laid-open No. H09-194585);
(9) a copolymer selected from at least one of methacrylic acid esters or acrylic acid esters such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, stearyl methacrylate, benzyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, stearyl acrylate, and benzyl acrylate, at least one of polymerizable monomers having a basic group such as acrylamide, methacrylamide, N-methylolamide, vinylimidazole, vinylpyridine, and a monomer having an amino group and a polycaprolactone skeleton, and at least one of styrene, a styrene derivative, and another polymerizable monomer (Japanese unexamined patent application, first publication No. Hei 01-164429);
(10) a carbodiimide type pigment dispersant containing a basic group (International publication WO 04/000950);
(11) a block copolymer comprising a block having a basic group such as a tertiary amino group or a quaternary ammonium salt and a block having no functional group (see the description of Japanese patent laid-open No. 2005-55814);
(12) a pigment dispersant obtained by subjecting a polyallylamine to a Michael addition reaction with a polycarbonate compound (Japanese patent application laid-open No. H09-194585);
(13) carbodiimide compounds each having at least one polybutadiene chain and a basic nitrogen-containing group (Japanese patent laid-open No. 2006-257243);
(14) carbodiimide compounds each having at least one side chain having an amide group and a basic nitrogen-containing group in the molecule (Japanese patent application laid-open No. 2006-176657);
(15) a polyurethane compound having a structural unit having an ethylene oxide chain and a propylene oxide chain and having an amino group quaternized by a quaternizing agent (jp 2009-175613 a);
(16) a compound obtained by reacting an isocyanate group of an isocyanate compound having an isocyanurate ring in a molecule with an active hydrogen group of a compound having an active hydrogen group in a molecule and having a carbazole ring and/or an azobenzene skeleton, wherein the number of carbazole rings and azobenzene skeleton in the molecule is 15 to 85% relative to the total of an isocyanate group derived from the isocyanate compound having an isocyanurate ring, and a urethane bond and a urea bond generated by the reaction of the isocyanate group and the active hydrogen group (Japanese patent application No. 2009-220836);
(17) graft copolymers in which polyether or polyester side chains are introduced into an acrylate polymer having amino groups.
Among the above-mentioned basic group-containing polymer pigment dispersants, the basic group-containing polyurethane pigment-based polymer pigment dispersants, the basic group-containing polyester polymer pigment dispersants, and the basic group-containing acrylic polymer pigment dispersants are more preferable, and the amino group-containing polyurethane pigment-based polymer pigment dispersants, the amino group-containing polyester polymer pigment dispersants, and the amino group-containing acrylic polymer pigment dispersants are still more preferable. Among the above-mentioned basic group-containing polymeric pigment dispersants, a polymeric pigment dispersant having a basic group (amino group) selected from at least one of a polyester chain, a polyether chain, and a polycarbonate chain is particularly preferable.
In the coloring composition of the present invention, the pigment dispersant is preferably 1 to 200 parts by mass, more preferably 5 to 100 parts by mass, based on 100 parts by mass of the pigment.
(pigment dispersing aid)
The coloring composition of the present invention preferably contains a pigment dispersion aid represented by the following general formula (1) and/or (2), and/or a pigment dispersion aid as a sulfonated (optionally neutralized) of copper phthalocyanine, and/or a pigment dispersion aid as a sulfonated (optionally neutralized) of c.i. pigment yellow 138.
Figure BDA0002385965690000091
In which X and Y are the same or different and are optionally substituted by F, Cl, Br, NO2、CH3Or OCH3Substituted phenyl; m represents H, Na, K, NH4Or NR1R2R3R4(Here, R is1、R2、R3And R4The same or different, represent a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms optionally substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms optionally substituted with other substituents; m represents an integer of 1 or more.
The pigment dispersing aid is used for dispersing the pigment.
When the pigment is dispersed, the pigment dispersing aid and the pigment dispersant are used in combination, whereby excellent fluidity and stability over time (stability over time) can be obtained. Further, when the above-mentioned colored composition is used as a colored resist composition, a high optical density can be obtained.
In the above general formulae (1) and (2), X and Y are the same or different and each represents an optionally substituted group selected from F, Cl, Br and NO2、CH3Or OCH3A substituted phenyl group. M represents H, Na, K, NH4Or NR1R2R3R4。
"NR" related to the above general formulae (1) and (2)1R2R3R4”(M)，R1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms optionally substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms optionally substituted with other substituents. Here, examples of the saturated or unsaturated aliphatic hydrocarbon group include: alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and decyl; alkenyl groups such as vinyl, allyl, and 1-butenyl; alkynyl groups such as ethynyl and propynyl. Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group. Examples of the other substituent include a hydroxyl group, a halogen group, a carboxyl group, an amino group, a lower alkyl group (having 1 to 5 carbon atoms), and the like.
In addition, R is as defined above1、R2、R3And R4In (3), 1 or more of the substituents may be substituted with other substituents, or 2 or more of the substituents may be substituted with other substituents.
Further, "m" in the general formulae (1) and (2) is an integer of 1 or more.
In the above compounds (pigment dispersing aids), the compound represented by the general formula (1) is of the enol type, the compound represented by the general formula (2) is of the ketone type, and the pigment dispersing aid includes two compounds. That is, the pigment dispersion aid includes a case where the pigment dispersion aid is composed of a compound represented by the general formula (1) or (2) and a case where the pigment dispersion aid is composed of both compounds represented by the general formulae (1) and (2).
Such pigment dispersing aids are novel compounds, are not commercially available, and can be produced, for example, by the following method: the monoazo compound represented by the following formulae (3) to (30) is dissolved in concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid or a mixture thereof, heated at room temperature or at 80 to 90 ℃, diluted with a large amount of water to obtain a suspension, the suspension is filtered and washed with water, and the obtained cake is dried and pulverized.
Figure BDA0002385965690000111
Among these pigment dispersion aids, from the viewpoint that a colored resist composition that can be obtained has good fluidity and stability over time and a high optical density, preferred are: a compound represented by the following general formula (31) (a compound obtained by the above production method or the like, which is a monoazo compound represented by the above formula (3): enol type) wherein X in the above general formula (1) and/or (2) is 2, 5-dichlorophenyl group, and Y is phenyl group) and/or a compound represented by the following general formula (32) (a compound obtained by the above production method or the like, which is a ketone type) are used.
Figure BDA0002385965690000121
In the coloring composition of the present invention, the pigment dispersion aid is preferably 30 parts by mass or less, and more preferably 0.1 to 20 parts by mass, per 100 parts by mass of the pigment.
Even if the amount of the pigment dispersion aid is more than 30 parts by mass per 100 parts by mass of the pigment, the pigment dispersion effect may not be improved.
(organic solvent)
The coloring composition of the present invention preferably contains an organic solvent.
The organic solvent is preferably normal pressure (1.013 × 10)2kPa) at 70 to 300 ℃, an ester organic solvent, an ether ester organic solvent, a ketone organic solvent, an aromatic hydrocarbon organic solvent, a nitrogen-containing organic solvent, and the like.
As such a solvent, specifically, there can be exemplified: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ether ester organic solvents such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ketone organic solvents such as methyl isobutyl ketone, cyclohexanone, 2-heptanone, -butyrolactone, methyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, 3-methyl-3-methoxybutyl propionate, methyl acetate, butyl acetate, Ester organic solvents such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxyacetate, glycolic acid ester, and N-amyl formate, nitrogen-containing organic solvents such as N-methylpyrrolidone, N-dimethylformamide, and N, N-dimethylacetamide, and the like; these organic solvents may be used alone or in combination of two or more.
Among these organic solvents, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 2-heptanone, ethyl 2-hydroxypropionate, 3-methyl-3-methoxybutyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, n-pentyl formate, and the like are preferable from the viewpoint of boiling point, solubility, dispersibility, coatability, and the like, and propylene glycol monomethyl ether acetate is more preferable.
(other additives)
According to the method for producing the colored composition of the present invention, various additives such as a photopolymerization initiator, a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant and the like can be suitably used.
The photopolymerization initiator is not particularly limited, and for example, the following can be used: benzophenone, N ' -tetraethyl-4, 4' -diaminobenzophenone, 4-methoxy-4 ' -dimethylaminobenzophenone, benzil, 2-diethoxyacetophenone, benzoin methyl ether, benzoin isobutyl ether, benzil dimethyl acetal, α -hydroxyisobutyl benzophenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, tert-butylanthraquinone, 1-chloroanthraquinone, 2, 3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1, 4-naphthoquinone, 1, 2-benzoanthraquinone, 1, 4-dimethylanthraquinone, 2-phenylanthraquinone, triazine photopolymerization initiator, oxime ester photopolymerization initiator, and the like. These photopolymerization initiators may be used alone or in combination of two or more.
In the colored composition of the present invention, the photopolymerization initiator is preferably 0.1 to 10% by mass, more preferably 0.5 to 4% by mass, in terms of mass fraction, relative to the total solid content.
< method for producing coloring composition >
An example of a method for producing a colored composition using the above materials will be described.
A binder resin, carbon black, a pigment dispersant, a pigment dispersion aid, an organic solvent, and other additives are added to and mixed with the pigments of the respective colors as needed to obtain a mixture.
The obtained mixture is kneaded and dispersed by using various dispersing machines such as a roll mill, a kneader, a high-speed stirring apparatus, a bead mill, a ball mill, a sand mill, an ultrasonic dispersing machine, and a high-pressure dispersing machine to obtain pigment dispersion compositions of various colors.
Next, the pigment dispersion compositions of the respective colors obtained are blended in a predetermined combination so as to achieve pseudo-blackening, and if necessary, a binder resin, an organic solvent, and other additives are added, and the mixture is uniformly mixed by using a stirring device such as a high-speed stirrer, and then filtered by a filter to obtain the colored composition of the present invention. In the above production method, the binder resin may be added at the time of producing the pigment dispersion composition. In addition, the pigment dispersion may be added after the preparation of the pigment dispersion composition and at the time of the preparation of the coloring composition.
(Co-disperse)
Obtaining a mixture comprising: a mixed pigment obtained by blending each pigment so as to achieve pseudo-blackening, a pigment dispersant, a pigment dispersion aid, an organic solvent, an optional binder resin as required, and further optional other additives. The obtained mixture is kneaded and dispersed by using various dispersing machines such as a roll mill, a kneader, a high-speed stirring device, a bead mill, a ball mill, a sand mill, an ultrasonic dispersing machine, and a high-pressure dispersing machine to obtain a pigment dispersion composition.
Next, a binder resin, an organic solvent, and other additives are added to the obtained pigment dispersion composition as needed, and the mixture is uniformly mixed using a stirring device such as a high-speed stirrer, and then filtered through a filter to obtain the colored composition of the present invention. In the above production method, the binder resin may be added at the time of producing the pigment dispersion composition.
In addition, the pigment dispersion may be added after the preparation of the pigment dispersion composition and at the time of the preparation of the coloring composition.
The coloring composition of the present invention preferably has a viscosity of 2.0 to 20.0 mPas measured at 25 ℃.
When the viscosity is less than 2.0 mPas or more than 20.0 mPas, the coatability may be adversely affected.
The viscosity is measured by using an E-type viscometer (manufactured by eastern industries, ltd.) after the colored composition of the present invention is sealed in a glass bottle or the like (with a sealing plug) and stored for 1 day.
The coloring composition of the present invention preferably has a stability with time of 0.8 to 1.1.
If the stability with time is less than 0.8 or more than 1.1, coatability and developability may be adversely affected.
The stability with time is obtained by the following steps: the stability with time was determined by measuring the viscosity at 25 ℃ after the colored composition of the present invention was sealed in a glass bottle or the like (with a sealing plug) and stored at room temperature (25 ℃) for 1 day and the viscosity at 25 ℃ after the colored composition of the present invention was sealed in a glass bottle or the like and stored at 40 ℃ for 7 days using an E-type viscometer (manufactured by eastern Industrial Co., Ltd.) so as to (the viscosity after storage at 40 ℃ for 7 days)/(the viscosity after storage at room temperature for 1 day).
Next, an example in which the colored composition of the present invention is used as a colored resist composition will be described.
The colored resist composition of the present invention comprises the colored composition of the present invention.
The colored resist composition of the present invention is preferably obtained by: in addition to the colored composition of the present invention, various additives such as an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent are added as necessary.
< constituent Material of colored resist composition >
(coloring composition)
The colored resist composition of the present invention is produced by using the colored composition of the present invention.
The content of the colored composition of the present invention is preferably 20 to 90% by mass, and more preferably 30 to 80% by mass, based on the total solid content of the colored resist composition of the present invention.
(pigment dispersant)
As the pigment dispersant, those described above in the coloring composition of the present invention can be preferably used.
In the colored resist composition of the present invention, the content of the pigment dispersant is preferably 0.1 to 50 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total pigments used.
(Binder resin)
As the binder resin, those described in the coloring composition of the present invention can be preferably used.
In the colored resist composition of the present invention, the content of the binder resin is preferably 3 to 50% by mass in the solid content of the colored resist composition of the present invention.
(photopolymerization initiator)
The photopolymerization initiator is not particularly limited, and for example: benzophenone, N ' -tetraethyl-4, 4' -diaminobenzophenone, 4-methoxy-4 ' -dimethylaminobenzophenone, benzil, 2-diethoxyacetophenone, benzoin methyl ether, benzoin isobutyl ether, benzil dimethyl acetal, alpha-hydroxyisobutyl benzophenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, tert-butylanthraquinone, 1-chloroanthraquinone, 2, 3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1, 4-naphthoquinone, 1, 2-benzoanthraquinone, 1, 4-dimethylanthraquinone, 2-phenylanthraquinone, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholine-1-propanone, Triazine-based photopolymerization initiators, oxime ester-based photopolymerization initiators (e.g., 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethanone 1- (O-acetyloxime), etc.), and the like. These photopolymerization initiators may be used alone or in combination of two or more.
In the colored composition of the present invention, the photopolymerization initiator is preferably 0.1 to 10% by mass, more preferably 0.5 to 6% by mass in terms of mass fraction with respect to the total solid content.
(photopolymerizable monomer)
As the photopolymerizable monomer, an ethylenic (ethylenically) unsaturated compound or the like is used. The ethylenically unsaturated compound used herein is preferably a compound having 2 or more ethylenically unsaturated bonds in the molecule from the viewpoint of polymerizability, crosslinkability, and the like. These photopolymerizable monomers may be used alone or in combination of two or more.
(organic solvent)
As the organic solvent, those described in the coloring composition of the present invention can be preferably used.
In the colored resist composition of the present invention, the content of the organic solvent is preferably 5 to 90% by mass relative to the total amount of the colored resist composition of the present invention, from the viewpoints of solubility of each material, pigment dispersibility, coatability, and the like.
(other additives)
In the colored resist composition of the present invention, various additives such as a heat-blocking agent (heat-polymerization inhibitor), an ultraviolet absorber, an antioxidant, and the like can be suitably used as needed.
< method for producing colored resist composition of the invention >
The method for producing the colored resist composition of the present invention is an example of a preferred embodiment of the present invention, and the present invention is not limited thereto.
For example, the following method may be used: the colored composition of the present invention is added with a binder resin, a photopolymerizable compound, a photopolymerization initiator, an organic solvent, and other additives, and stirred and mixed using a stirring device or the like.
The colored resist composition of the present invention preferably has a viscosity of 1.0 to 30.0 mPas measured at 25 ℃.
When the viscosity is less than 1.0 mPas or more than 30.0 mPas, the coatability may be adversely affected.
The viscosity is measured using an E-type viscometer (manufactured by eastern industries, ltd.) after the colored resist composition of the present invention is sealed in a glass bottle or the like and stored for 1 day.
The colored resist composition of the present invention preferably has a stability with time of 0.8 to 1.2.
If the stability with time is less than 0.8 or more than 1.2, the coating developability may be adversely affected. The stability with time is obtained by the following steps: the stability with time was determined by measuring the viscosity at 25 ℃ after the colored composition of the present invention was sealed in a light-shielding glass bottle or the like and stored at a low temperature (5 ℃) for 1 day and the viscosity at 25 ℃ after the colored composition of the present invention was sealed in a light-shielding glass bottle or the like and stored at a low temperature (5 ℃) for 7 days using an E-type viscometer (manufactured by eastern Industrial Co., Ltd.) so as to obtain (viscosity after storage at 5 ℃ for 7 days)/(viscosity after storage at 5 ℃ for 1 day).
The colored resist composition of the present invention has an optical density (OD value) of preferably 1.00 or more, more preferably 1.20 or more, when a resist pattern having a thickness of 1 μm is formed.
When the optical density (OD value) is 1.25 or more, the light-shielding property is said to be sufficient.
The optical density (OD value) is a value measured by a Macbeth densitometer (TD-931, trade name, manufactured by Macbeth co., Ltd.) to form a resist pattern of only 1 μm using the colored resist composition of the present invention.
The solvent resistance of the colored resist composition of the present invention in forming a cured coating film having a thickness of 2 μm is preferably 0.6 or less, more preferably 0.5 or less, even more preferably 0.4 or less, particularly preferably 0.3 or less, and most preferably 0.2 or less.
Further, the above solvent resistance was obtained by immersing a cured coating film having a thickness of 2 μm in N-methylpyrrolidone heated to 100 ℃ and keeping it in an oven at 100 ℃ for 10 minutes; then, the absorbance of the above N-methylpyrrolidone was measured with a spectrophotometer (UV-2500PC), and the absorbance at the maximum peak was set as the value of the solvent resistance.
The colored composition and the colored resist composition of the present invention have the above-described characteristics, and therefore can be suitably used as a black matrix, a black column spacer, or a black partition material for an image display device, a touch panel, or the like.
Effects of the invention
The present invention provides a colored composition having excellent light-shielding properties and excellent solvent resistance, and a colored resist composition containing the colored composition.
Detailed Description
The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto without departing from the spirit and scope of the invention. In the present example, "part" and "%" represent "part by mass" and "% by mass", respectively, unless otherwise specified.
The materials of the coloring compositions used in examples 1 to 10 and comparative examples 1 to 3 are as follows.
< pigment >
P.V.23(C.I. pigment Violet 23)
P.V.29(C.I. pigment Violet 29)
P.V.32(C.I. pigment Violet 32)
P.Y.139(C.I. pigment yellow 139)
P.Y.185(C.I. pigment yellow 185)
P.O.16(C.I. pigment orange 16)
P.O.64(C.I. pigment orange 64)
P.R.254(C.I. pigment Red 254)
P.B.60(C.I. pigment blue 60)
P.B.15:6(C.I. pigment blue 15:6)
< carbon Black >
TPK1104R (manufactured by CABOT, oil absorption 38ml/100g, pH 2.7)
< adhesive resin >
BzMA/MAA (alkali soluble resin, methyl benzyl methacrylate/methacrylic acid copolymer, theoretical acid value of 120mgKOH/g, mass average molecular weight of 10000)
< pigment dispersant >
BYK-LPN-22102 (acrylic block copolymer having a segment having a pigment affinity group and a segment having an adhesive compatibility group, manufactured by ビックケミー Co., Ltd.)
< pigment Dispersion aid >
30ml of concentrated sulfuric acid was charged into a 100ml Erlenmeyer flask, 10g of pigment Red 2 (the compound represented by the above formula (3) and/or (4)) was charged while stirring with a magnetic stirrer, and the mixture was stirred at room temperature for 30 minutes. A mixture of 50g of water and 50g of ice was added to a 1L beaker, and the above reaction mixture was poured into the ice water and stirred with a magnetic stirrer for 30 minutes. This was filtered under reduced pressure, washed with water, and the resulting solid was dried to obtain 12g of a pigment dispersion aid 1 (a compound represented by the above general formula (31) and/or (32): M ═ H).
< organic solvent >
PGMEA (propylene glycol monomethyl ether acetate)
The materials of the colored resist compositions used in examples 11 to 20 and comparative examples 4 to 6 are as follows.
< adhesive resin >
SPC-3500 (alkali-soluble resin containing carbon ═ carbon unsaturated bond, theoretical acid value of 60mgKOH/g, mass average molecular weight of 11000)
< photopolymerization initiator >
Irgacure (イルガキュア)907 (manufactured by BASF, 2-methyl-1 [4- (methylthio) phenyl ] -2-morpholinopropan-1-one) and Irgacure OXE02 (manufactured by BASF, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethanone 1- (O-acetyloxime)) in a 1: 1 mixture
< photopolymerizable monomer >
DPEHA (photopolymerizable compound, dipentaerythritol hexaacrylate)
< organic solvent >
PGMEA (propylene glycol monomethyl ether acetate)
< preparation of coloring compositions of examples 1 to 10 and comparative examples 1 to 3 >
The coloring compositions of examples 1 to 10 and comparative examples 1 to 3 were prepared by mixing the respective materials so as to have the composition shown in Table 1 (the amount of each material used in Table 1 is mass%), and kneading the mixture by a bead mill for one day and night.
< preparation of colored resist compositions of examples 11 to 20 and comparative examples 4 to 6 >
The colored resist compositions of examples 11 to 20 and comparative examples 4 to 6 were obtained by uniformly mixing the colored resist compositions of examples 1 to 10 and comparative examples 1 to 3 with other materials so as to have the composition shown in Table 2 (the amount of each material used in Table 2 is defined as mass%), and then filtering the mixture through a filter having a pore diameter of 3 μm.
(evaluation test)
The colored compositions obtained in examples 1 to 10 and comparative examples 1 to 3, and the colored resist compositions obtained in examples 11 to 20 and comparative examples 4 to 6 were evaluated for fluidity and stability with time by the following methods, and the results are shown in tables 1 and 2.
Further, the colored resist compositions obtained in examples 11 to 20 and comparative examples 4 to 6 were applied to form resist patterns, and the optical density and solvent resistance thereof were evaluated, and the results are shown in Table 2.
< fluidity >
For the colored compositions obtained in examples 1 to 10 and comparative examples 1 to 3, each of the compositions was sealed with a sealing plug in a glass bottle, stored at room temperature (25 ℃) for 1 day, and then measured for viscosity [ mPas ] at 25 ℃ using an E-type viscometer (manufactured by Toyobo industries Co., Ltd.) to evaluate fluidity.
The colored resist compositions obtained in examples 11 to 20 and comparative examples 4 to 6 were each subjected to sealing with a sealing plug in a light-shielding glass bottle, stored at a low temperature (5 ℃) for 1 day, and then measured for viscosity [ mPas ] at 25 ℃ using an E-type viscometer (manufactured by Toyobo industries, Ltd.) to evaluate fluidity.
< stability with time >
The colored compositions obtained in examples 1 to 10 and comparative examples 1 to 3 were each collected in a glass bottle, and the viscosity at 25 ℃ after storing the colored composition of the present invention in a glass bottle or the like at room temperature (25 ℃) for 1 day and the viscosity at 25 ℃ after storing the colored composition of the present invention in a glass bottle or the like at 40 ℃ for 7 days were measured using an E-type viscometer (manufactured by eastern industries co., ltd.), and the viscosities were determined as (viscosity after storing at 40 ℃ for 7 days)/(viscosity after storing at room temperature for 1 day).
The viscosities at 25 ℃ after storing the colored resist compositions obtained in examples 11 to 20 and comparative examples 4 to 6 at a low temperature (5 ℃) for 1 day with a sealing plug in a light-shielding glass bottle or the like were measured using an E-type viscometer (manufactured by eastern industries co., ltd.), and the viscosities at 25 ℃ after storing the colored resist compositions of the present invention at a low temperature (5 ℃) for 7 days with a sealing plug in a light-shielding glass bottle or the like were determined as (viscosity after storing at 5 ℃ for 7 days)/(viscosity after storing at 5 ℃ for 1 day).
< optical Density (OD value) >
The colored resist compositions of examples 11 to 20 and comparative examples 4 to 6 were applied onto a glass substrate by a spin coater so that the film thickness became 1 μm, prebaked at 100 ℃ for 3 minutes, exposed to light using a high-pressure mercury lamp, and further baked at 230 ℃ for 30 minutes to obtain a black resist pattern formed only in the solid portion. The optical density (OD value) of the black resist pattern in each solid portion was measured with a Macbeth densitometer (TD-931, trade name, manufactured by Macbeth corporation).
< solvent resistance >
The colored resist compositions of examples 11 to 20 and comparative examples 4 to 6 were applied onto a glass substrate by a spin coater so that the film thickness became 1 μm, prebaked at 100 ℃ for 3 minutes, exposed to a high-pressure mercury lamp, and postbaked at 230 ℃ for 30 minutes to obtain a cured coating film formed only in the solid portion.
The obtained cured coating film of each solid portion was immersed in N-methylpyrrolidone heated to 100 ℃ and kept in an oven at 100 ℃ for 10 minutes; then, the absorbance of the above N-methylpyrrolidone was measured with a spectrophotometer (UV-2500PC), and the absorbance at the maximum peak was set as the value of the solvent resistance.
[ Table 1]
Figure BDA0002385965690000221
[ Table 2]
Figure BDA0002385965690000222
The colored compositions and colored resist compositions according to examples have confirmed: excellent in fluidity and stability with time.
Further, the colored resist compositions according to the examples have confirmed: an OD value of 1.25 or more and a solvent resistance of 0.60 or less, and is excellent in both light-shielding properties and solvent resistance.
The colored composition and the colored resist composition of the embodiments have the above-described characteristics, and therefore can be suitably used as a black matrix, a black column spacer, or a black partition material of an image display device, a touch panel, or the like.
On the other hand, none of the colored compositions and the colored resist compositions according to comparative examples had excellent light-shielding properties and excellent solvent resistance.
Industrial applicability
The present invention provides a colored composition having excellent light-shielding properties and excellent solvent resistance, and a colored resist composition containing the colored composition.

Claims (4)

1. A coloring composition characterized by comprising, as a main component,
which comprises a pigment and a binder resin, and
the pigment comprises: at least one selected from the group consisting of c.i. pigment orange 16 and c.i. pigment yellow 139, and c.i. pigment blue 60.
2. The coloring composition according to claim 1, wherein the pigment further comprises one or more selected from the group consisting of c.i. pigment violet 23 and c.i. pigment violet 29.
3. A colored resist composition produced by using the colored composition according to claim 1 or 2.
4. The colored composition according to claim 1 or 2 or the colored resist composition according to claim 3, which is used as a black matrix, a black column spacer, or a black partition material.
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